After a season that defied expectations and brought playoff basketball back to Scotiabank Arena, the Toronto Raptors are moving quickly to secure their leadership. General manager Bobby Webster and head coach Darko Rajakovic are both expected to receive extension offers in the coming weeks, signaling a commitment to continuity following the team’s first winning campaign in four years.
With both men entering the final year of their contracts, the Raptors are keen to avoid “lame duck” status for their front office and bench, especially after pushing the Cleveland Cavaliers to a grueling seven games in the first round.
Rewarding the Rebuild
The 2025/26 season was widely viewed as an “extended job interview” for Webster, who took full control of basketball operations following Masai Ujiri’s departure to Dallas. The results were undeniable:
- Record: A solid 46-36 finish.
- Development: The successful integration of young talents like Scottie Barnes, Ja’Kobe Walter, and rookie standout Collin Murray-Boyles.
- Coaching: Darko Rajakovic secured his first winning season and playoff appearance since taking the helm in 2023, proving his player-development systems could translate to post-season grit.
The “Mavericks” Factor
A sense of urgency has been injected into these negotiations due to Masai Ujiri’s new role as president of the Dallas Mavericks. Speculation had swirled that Ujiri might attempt to lure Webster to Texas to reunite their championship-winning partnership.
However, sources close to the situation have dismissed the idea. Webster has reportedly enjoyed his role as the primary decision-maker in Toronto and is unlikely to return to a secondary role under Ujiri.
The Real Threat to Depth:
While Webster appears set to stay, the Raptors’ scouting and evaluation staff are under fire. Ujiri is expected to target:
- Dan Tolzman: The Assistant GM and player personnel expert is considered a top candidate for the Mavericks’ GM role.
- Patrick Engelbrecht & Curtis Crawford: Key figures in Toronto’s global scouting network who may be tempted by a move to Dallas.
A Conservative Deadline, A Long-Term Vision
The report by Michael Grange sheds light on why the Raptors were surprisingly quiet at the trade deadline. Despite having Jaren Jackson Jr. “very much on their radar,” Webster chose not to enter a bidding war with the Utah Jazz.
This conservative approach was reportedly supported by MLSE president Keith Pelley, who placed no immediate pressure on Webster to make a “splash” move. This lack of pressure was the first major hint that the organization was already satisfied with Webster’s long-term trajectory for the franchise.
The Bottom Line
By locking in Webster and Rajakovic, the Raptors are betting that the current core—led by an All-Star caliber Scottie Barnes—is on the right path. With the “lame duck” narrative put to rest, Webster can now turn his full attention to a pivotal 2026 offseason, where the Raptors hold the 19th overall pick and the flexibility to continue their climb back to Eastern Conference elite status.
Front Office Watch: While Webster handles his own deal with MLSE, he is expected to personally lead the negotiations to keep Rajakovic in Toronto for the long haul.
